Trifluoroacetic acid → HCID 20646773, compound

HRID 324286Notes

Reaction equation

HRID 324286 reaction equation
C(OC([NH:8][C@@H:9]([C:23]([OH:25])=[O:24])[C:10]([S:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:12])[CH3:11])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][S:13][C:10]([CH3:12])([CH3:11])[C@H:9]([C:23]([OH:25])=[O:24])[NH2:8])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 7018786Boc-D-Pen(Mob)-OH

Product 1

HCID 20646773HCID 20646773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The N-t-butoxycarbonyl-S-(4-methoxybenzyl)-D-penicillamine (5.0 g, 13.5 mmol) is dissolved in 40 mL of methylene chloride and cooled to 0° C. in an ice bath. Trifluoroacetic acid (18.5 g, 162 mmol) is added next, and the resulting mixture is stirred at 0° C. for 1 hour. The reaction mixture is warmed to room temperature and stirred until the starting material disappeared by TLC and mass spec (3 h.). The trifluoroacetic acid and methylene chloride are evaporated under reduced pressure to give the desired product.

Workup

  1. temperatureThe reaction mixture is warmed to room temperature
  2. stirringstirred until the starting material
  3. customdisappeared by TLC and mass spec (3 h.)
  4. customThe trifluoroacetic acid and methylene chloride are evaporated under reduced pressure

Sources & evidence

ORD record
ord-3836a261e2cf46ef9d6ac5c4bb42edf6
Source dataset
uspto-grants-2001_04
Patent number
US06218389B1

Reaction notes

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